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324442

Sigma-Aldrich

O2,2′-Cyclouridine

99%

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About This Item

Empirical Formula (Hill Notation):
C9H10N2O5
CAS Number:
3736-77-4
Molecular Weight:
226.19
EC Number:
223-107-6
MDL number:
MFCD00004945
UNSPSC Code:
12352100
PubChem Substance ID:
24859440
NACRES:
NA.22

assay

99%

optical activity

[α]19/D −21°, c = 4 in H2O

mp

248-251 °C (lit.)

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@@H]2[C@@H](OC3=NC(=O)C=C[N@@H]23)[C@@H]1O

InChI

1S/C9H10N2O5/c12-3-4-6(14)7-8(15-4)11-2-1-5(13)10-9(11)16-7/h1-2,4,6-8,12,14H,3H2/t4-,6-,7+,8-/m1/s1

InChI key

UUGITDASWNOAGG-CCXZUQQUSA-N

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Application

Research tool for antiviral and anticancer studies.[1]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
03507TH
15722CU
14221DF
12325MN
07516JS

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Vladimir I Timofeev et al.
Acta crystallographica. Section F, Structural biology and crystallization communications, 63(Pt 10), 852-854 (2007-10-03)
Uridine phosphorylase (UPh; EC 2.4.2.3) is a member of the pyrimidine nucleoside phosphorylase family of enzymes which catalyzes the phosphorolytic cleavage of the C-N glycoside bond of uridine, with the formation of ribose 1-phosphate and uracil. This enzyme has been
Christopher S Theile et al.
Chemical communications (Cambridge, England), 48(45), 5587-5589 (2012-04-26)
Here we present new routes for the efficient syntheses of 6,5'-(S)- and 6,5'-(R)-cyclouridine. The syntheses utilize readily accessible uridine as a starting material. This route to the R diastereomer is significantly more efficient than previous synthetic efforts, allowing us to
A K Drabikowska et al.
Biochemical pharmacology, 36(23), 4125-4128 (1987-12-01)
Two series of 5-substituted uracil N(1)-acyclonucleosides, each with a different acyclic chain, were examined as inhibitors of uridine phosphorylase from rat intestinal mucosa, and several against the enzyme from Ehrlich ascites cells. In addition, several 5-substituted analogues of 2,2'-anhydrouridine were
Ying Fu et al.
Acta crystallographica. Section C, Crystal structure communications, 69(Pt 3), 282-284 (2013-03-06)
2,2'-Anhydro-1-(3',5'-di-O-acetyl-β-D-arabinofuranosyl)uracil, C13H14N2O7, was obtained by refluxing 2',3'-O-(methoxymethylene)uridine in acetic anhydride. The structure exhibits a nearly perfect C4'-endo ((4)E) conformation. The best four-atom plane of the five-membered furanose ring is O-C-C-C, involving the C atoms of the fused five-membered oxazolidine ring
Aldrichimica Acta, 20, 52-52 (1987)

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